Sulphurized compound of phenol



- hol or acetone.

Reissued Jan. 27, 1931 UNITED STATES PATENT OFFICE ALFRED THAUSS, OI DENTZ, NEAR COLOGNE, AND ALFRED- GNNTHER, OF COLOGNE, GERMANY, ASSIGNORS, BY MESNE ASSIGNMENTS, TO GENERAL ANILINE WORKS, INC., OF NEW YORK, N. Y., A CORPORATION OF DELAWARE SULPHURIZED COMPOUND 0F PHENOL No Drawing. Original No. 1,450,463, dated April 3, 1928, Serial No. 490,747, filed August 8, 192 1. Application for reissue filed October 31, 1930. Serial No. 492,610.

This invention relates to the manufacture of new mordants. They consist of new sulphurized compounds of phenol, its homoogues and its substitution products, such as cresols, chlorphenols, and the like, and are obtained by heating phenol or its homologues or substitution products with aqueous caustic alkali and sulfur, in practice in quantities larger than the'molecular proportions. The new sulfur derivatives are easily absorbed by undyed cotton fiber and act as mordants for basic colors. The dyeings thus obtained are faster to washing and to light than those produced on tannin. The new compounds are generally yellowish powders.

The invention is illustrated by the following example, the parts being by weight 26 parts of orthochlorphenol are dissolved in 20 parts of hot water and 8.5 parts of sodium hydroxid. On the addition of 10 parts of sulfur i. e., about 1 mols of sulfur to each mol of orthochlorphenol used, this solution is heated at boiling in a vessel provided with a reflux condenser. The resinous reaction i product thus produced, which solidifies to a brittle, vitreous mass on cooling, is separated from the aqueous liquor, dissolved in 15 parts of sodium carbonate and 200 parts of hot water, and finally salted out with sodium sulfate. The greenish paste thus obtained is dried by heating in vacuo until after cooling a test turns solid and pulverulent. The dry product is readily soluble at room temperature in organic solvents, such as ethyl alco- The sodium salt is soluble in cold and easily soluble in warm water.

Analogous compounds are obtained when orthochlorphenol is replaced by the paraproduct, the phenol itself, the cresols, the dior polychloror the corresponding bromphenols.

For dyeing purposes the product prepared according to the above example from orthoe chlorphenol is dissolved, for example, in sodium carbonate solution.

Cotton is mordanted with 5 per cent of this It is remarkable that basic dyestuffs, such as rhodamin B extra, methylviolet B,

auramin O and others possess after this process of fixing the same shades as those produced by the tannin method.

The new mordants may be added to a dye bath containing asubstantive cotton dyestuif and a sulfur dyestuff the'dyeing being aftertreated with a basic dyestuff. The colors hereby obtained are better fixed or more in tense than those topped according tomethods hitherto known.

We claim:

1. The hereindescribed new sulphurized compounds of phenols whichare obtainable by boiling about 1 mol of a phenol with aqueous caustic alkali and about 1 mol of sulfur whereby a resinous reaction product which solidifies to a brittle vitreous mass on cooling is produced, which compounds after purification are generally yellowish powders eing mordants for fixing basic dyes on cotton and being soluble in alcohol and acetone, substantially as described.

2. The hereindescribed new sulphurized compound of orthochlorphenol which is obtainable by boiling about 1 mol of orthochlorphenol with aqueous caustic alkali and about 1 mol'of sulfur whereby a resinous reaction product which solidifies to a brittle vitreous mass on cooling is produced, which compound after purification is a yellowish powder being a mordant for fixing basic dyes on cotton and being soluble in alcohol and acetone, substantially as described.

In testimony whereof we aflix our signatures.

- ALFRED THAUSS.

ALFRED GU'NTHER. 

